Diethyl Malonate → HCID 21876400, compound

HRID 724123Notes

Reaction equation

HRID 724123 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][OH:18])=[CH:12][CH:11]=2)[C:3]=1[N+:19]([O-:21])=[O:20].[C:22]([O:30][CH2:31][CH3:32])(=[O:29])[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].[OH-].[Na+]>CC(C)=O>[OH:18][CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:4]2[N:5]=[C:6]([CH3:8])[N:7]=[C:2]([CH:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:22]([O:30][CH2:31][CH3:32])=[O:29])[C:3]=2[N+:19]([O-:21])=[O:20])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 14798Sodium HydroxideHCID 21876505HCID 21876505, compound

Product 1

HCID 21876400HCID 21876400, compoundYield 116.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 2-{4-[(6-chloro-2-methyl-5-nitro-4-pyrimidinyl)amino]phenyl}ethanol (step 1, 2.0 g, 6.48 mmol) in acetone (61 ml) was added diethyl malonate (1.53 g, 9.54 mmol) at 0° C., then aqueous NaOH solution (11N, 2 ml, 22 mmol) was added dropwise over 20 min. After addition, the mixture was stirred at room temperature for 1 h. The reaction was quenched with water (120 ml), and the pH value was adjusted to 8.0 by addition of acetic acid. The whole was extracted with ethyl acetate (100 ml×3). The organic layer was washed with brine (50 ml), dried (MgSO4), and concentrated. Removal of excess diethyl malonate by azetropical distillation with toluene afforded 3.26 g (72%) of the title compound as a brown oil.

Workup

  1. additionAfter addition
  2. customThe reaction was quenched with water (120 ml)
  3. additionthe pH value was adjusted to 8.0 by addition of acetic acid
  4. extractionThe whole was extracted with ethyl acetate (100 ml×3)
  5. washThe organic layer was washed with brine (50 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customRemoval of excess diethyl malonate
  9. distillationby azetropical distillation with toluene

Sources & evidence

ORD record
ord-7cc4bef6db514d5e8611e5f4255df351
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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